Top Caribbean Private Sightseeing Tours

Q: Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include: Private Eleuthera Island: Swim With Pigs, Turtles & Stingrays Private Exuma Cays Day: Iguana, Shark, Pigs, Sandbar & Lunch 5-Day Private Tour in The Bahamas with Pickup Yacht YES DARLING - Private Boat St Martin, St Barth & Anguilla St Martin Gd-Case, Private Romantic Cruise 4 days View all Tours with Instant Confirmation →

Q: Got any more Caribbean trip ideas?

We sure do. Check out our curated lists of hand-picked Caribbean Tours. Top 10 Caribbean 2026 Senior-friendly tours Caribbean The best tours and activities for culture lovers in Caribbean Top Day Trips from Caribbean Things to do in Caribbean this summer View all Caribbean Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Caribbean?

Based on our sales data over the past year, the most popular styles of tours and activities in Caribbean are: Caribbean Luxury & Special Occasions Caribbean Luxury Tours Caribbean Tours & Sightseeing Caribbean Shore Excursions Caribbean Port Transfers View all tour styles in Caribbean →

Family Catamaran + Diving Lessons for kids + Paddel Board

Give your family more than a tour—give them a memory they’ll talk about forever. Step aboard your private sailing catamaran in Punta Cana, reserved exclusively …More

Punta Cana, Dominican Republic

4.3 (7)

Family Catamaran + Diving Lessons for kids + Paddel Board

Give your family more than a tour—give them a memory they’ll talk about forever. Step aboard your private sailing catamaran in Punta Cana, reserved exclusively...

3 hours Hotel pickup offered Free Cancellation

4.3 (7)

from
$900

Half Day Private Tour to Icacos Island Beach & Snorkeling

Our Half Day Tour is perfect for those who want to enjoy the best beaches on the East Coast of Puerto Rico in a short …More

5.0 (2)

Half Day Private Tour to Icacos Island Beach & Snorkeling

Our Half Day Tour is perfect for those who want to enjoy the best beaches on the East Coast of Puerto Rico in a short...

4 hours Free Cancellation

5.0 (2)

from
$900

Charter our tour services for your private event, weddings, birthday or company trip. We customize all trips per your specifications. Our basic package includes a …More

4.5 (6)

Private St Thomas Customized Tour

Charter our tour services for your private event, weddings, birthday or company trip. We customize all trips per your specifications. Our basic package includes a...

5 hours Hotel pickup offered Free Cancellation

4.5 (6)

from
$899

Half or Full-Day Private Boat Charter from St. John or St. Thomas

Depart on your private island‑hopping adventure with Bonus Time Charters aboard one of our 29' or 32' Power Catamaran and explore the very best of …More

5.0 (156)

Half or Full-Day Private Boat Charter from St. John or St. Thomas

Depart on your private island‑hopping adventure with Bonus Time Charters aboard one of our 29' or 32' Power Catamaran and explore the very best of...

3 hours 30 minutes Free Cancellation

5.0 (156)

from
$895

Join us for a personalized 3 hour tour of Bermuda! Led by expert local guides, you’ll explore Bermuda, visiting stunning hotspots while traveling in the …More

5.0 (7)

Bermudaful Island 3 Hours Private Tour

Join us for a personalized 3 hour tour of Bermuda! Led by expert local guides, you’ll explore Bermuda, visiting stunning hotspots while traveling in the...

3 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$895

27ft Dream Life Private Charter in Nassau

With this private tour you have the flexibility to experience The Bahamas your way without being grouped together with strangers. …More

5.0 (6)

27ft Dream Life Private Charter in Nassau

With this private tour you have the flexibility to experience The Bahamas your way without being grouped together with strangers....

4 hours Free Cancellation

5.0 (6)

from
$890

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Turks and Caicos Islands as you make …More

Private Tour 9-Hr in Turks and Caicos Islands

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Turks and Caicos Islands as you make...

9 hours Hotel pickup offered

from
$882

Private Cruise Party with Drinks and Snorkeling in Punta Cana

Welcome aboard our unforgettable party boat activity with snorkeling, open bar and a stop at a natural pool! Upon arrival at the port, our team …More

Punta Cana, Dominican Republic

4.9 (15)

Private Cruise Party with Drinks and Snorkeling in Punta Cana

Welcome aboard our unforgettable party boat activity with snorkeling, open bar and a stop at a natural pool! Upon arrival at the port, our team...

3 hours Hotel pickup offered Free Cancellation

4.9 (15)

from
$880

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Turks and Caicos Islands as you make …More

Private Tour Charter Deep Sea Fishing on Wahooter's

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Turks and Caicos Islands as you make...

7 hours Hotel pickup offered

from
$876

Experience the thrill of driving yourself on a guided Jeep 4x4 Adventure Tour on the island of Jost Van Dayke in the Virgin Islands We …More

Tortola, British Virgin Islands

3.0 (1)

Jost Van Dyke Jeep 4x4 Adventure Tour

Experience the thrill of driving yourself on a guided Jeep 4x4 Adventure Tour on the island of Jost Van Dayke in the Virgin Islands We...

4 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$875

Exotic half day private charters to Rose Island, Pigs and Turtles

Experience a one-of-a-kind adventure under the guidance of your own private captain. Where the open seas become a canvas for unforgettable memories and a deeper …More

5.0 (34)

Exotic half day private charters to Rose Island, Pigs and Turtles

Experience a one-of-a-kind adventure under the guidance of your own private captain. Where the open seas become a canvas for unforgettable memories and a deeper...

4 hours Free Cancellation

5.0 (34)

from
$860

Coral Sunset Sail with 3 Course Dinner in Aruba

Enjoy a private romantic sunset cruise and 3 course dinner for two or for a for a group of up to 6 friends. We offer …More

Palm - Eagle Beach, Aruba

4.8 (13)

Coral Sunset Sail with 3 Course Dinner in Aruba

Enjoy a private romantic sunset cruise and 3 course dinner for two or for a for a group of up to 6 friends. We offer...

3 hours Hotel pickup offered Free Cancellation

4.8 (13)

from
$859

Rose Island: Private Snorkeling, Fishing, and Swimming with Pigs

Fun all day boating experience with a friendly staff who is will to go above and beyond to make your vacation one to remember. From …More

4.8 (36)

Rose Island: Private Snorkeling, Fishing, and Swimming with Pigs

Fun all day boating experience with a friendly staff who is will to go above and beyond to make your vacation one to remember. From...

4 hours Free Cancellation

4.8 (36)

from
$850

Cayman Private Luxury Charters - Stingray City, Snorkel, & More

We provide a variety of tour options accommodating guests that'd like to make one stop or see it all. Our team are all born and …More

Grand Cayman, Cayman Islands

4.9 (81)

Cayman Private Luxury Charters - Stingray City, Snorkel, & More

We provide a variety of tour options accommodating guests that'd like to make one stop or see it all. Our team are all born and...

2 to 6 hours Free Cancellation

4.9 (81)

from
$850

Private Catamaran Cruise with Slide & unlimited drinks

Set sail on a private catamaran experience designed exclusively for you and your group. Cruise across turquoise Caribbean waters while enjoying music, drinks, and a …More

Punta Cana, Dominican Republic

5.0 (167)

Private Catamaran Cruise with Slide & unlimited drinks

Set sail on a private catamaran experience designed exclusively for you and your group. Cruise across turquoise Caribbean waters while enjoying music, drinks, and a...

3 hours Hotel pickup offered Free Cancellation

5.0 (167)

from
$850

Why plan your trip with us? At Otta Control Charters we make it our mission to ensure our guest relax and take a break from …More

Grand Cayman, Cayman Islands

5.0 (20)

Private Boat Tour in Cayman Islands

Why plan your trip with us? At Otta Control Charters we make it our mission to ensure our guest relax and take a break from...

3 hours Free Cancellation

5.0 (20)

from
$850

Discover the beauty of Cayo Icacos, Puerto Rico, on a private boat excursion departing from Marina Puerto del Rey in Fajardo. Enjoy crystal-clear turquoise waters, …More

Fajardo, Puerto Rico

5.0 (18)

Fajardo Puerto Rico Private Boat Tour to Cayo Icacos

Discover the beauty of Cayo Icacos, Puerto Rico, on a private boat excursion departing from Marina Puerto del Rey in Fajardo. Enjoy crystal-clear turquoise waters,...

4 hours Free Cancellation

5.0 (18)

from
$850

St Thomas Half Day Private Tour (1-10 ppl)

This tour caters to your group only. You get a vehicle just for your group for the whole day. It offers the flexibility of choosing …More

Cruz Bay, US Virgin Islands

4.6 (12)

St Thomas Half Day Private Tour (1-10 ppl)

This tour caters to your group only. You get a vehicle just for your group for the whole day. It offers the flexibility of choosing...

4 hours Hotel pickup offered Free Cancellation

4.6 (12)

from
$850

Providenciales offers so many amazing things to do and beautiful places to see, chose from our favourite activities and destinations or suggest your own and …More

3.7 (6)

Private Tailor-Made Safari Tour

Providenciales offers so many amazing things to do and beautiful places to see, chose from our favourite activities and destinations or suggest your own and...

4 hours Hotel pickup offered Free Cancellation

3.7 (6)

from
$850

Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

Outtaheretours is led by a team of Sailors,Divers, Instructors and Seaman with many years working in Aquatic Tourism. We are positive that nothing short of …More

Fajardo, Puerto Rico

5.0 (11)

Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

Outtaheretours is led by a team of Sailors,Divers, Instructors and Seaman with many years working in Aquatic Tourism. We are positive that nothing short of...

3 to 5 hours Free Cancellation

5.0 (11)

from
$850

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Caribbean Private Sightseeing Tours?

What are the best kid-friendly options for Caribbean Private Sightseeing Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Private Sightseeing Tours are:

View all kid-friendly Tours →

Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Which Caribbean Private Sightseeing Tours have Free Cancellation?

Caribbean Private Sightseeing Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Caribbean Private Sightseeing Tours have Hotel Pickup?

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Caribbean trip ideas?

What are the most popular styles of Tours and Activities in Caribbean?